Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction

The action of 2-(1-arylethylidene)malononitriles on 2-nitro-1H-benzo[f]chromenes in the presence of Et3N and MoO3•2H2O results in naphtho[2,1-b]furans containing an allylidenemalononitrile unit in the α-position. The reaction proceeds with contraction of the pyran ring via a cascade carba-Michael ad...

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Bibliografische gegevens
Hoofdauteurs:	Demidov, O. P., Демидов, О. П.
Formaat:	Статья
Taal:	English
Gepubliceerd in:	2024
Onderwerpen:	2-Nitro-1H-benzo[f]chromenes Divergent transformations Naphtho[2,1-b]furans Pyran ring contraction
Online toegang:	https://dspace.ncfu.ru/handle/20.500.12258/26909
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id	ir-20.500.12258-26909
record_format	dspace
spelling	ir-20.500.12258-269092024-03-13T12:29:27Z Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction Demidov, O. P. Демидов, О. П. 2-Nitro-1H-benzo[f]chromenes Divergent transformations Naphtho[2,1-b]furans Pyran ring contraction The action of 2-(1-arylethylidene)malononitriles on 2-nitro-1H-benzo[f]chromenes in the presence of Et3N and MoO3•2H2O results in naphtho[2,1-b]furans containing an allylidenemalononitrile unit in the α-position. The reaction proceeds with contraction of the pyran ring via a cascade carba-Michael addition/retro-oxa-Michael reaction/tautomerization/SN2/oxidation process. In contrast, the reaction of 2-nitro-1H-benzo[f]chromenes with the cyclic Knoevenagel adduct derived from 1-indanone and malononitrile leads to dihydroindeno[1,2-c]xanthenes. The possibility of further transformations of naphtho[2,1-b]furan derivatives as useful precursors and their optical properties were also investigated. 2024-03-13T12:26:53Z 2024-03-13T12:26:53Z 2024 Статья Korzhenko, K.S., Yushkova, A.S., Osipov, D.V., Rashchepkina, D.A., Demidov, O.P., Osyanin, V.A. Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction // Organic Letters. - 2024. - 26 (7). - pp. 1310-1315. - DOI: 10.1021/acs.orglett.3c03879 http://hdl.handle.net/20.500.12258/26909 en Organic Letters application/pdf application/pdf
institution	СКФУ
collection	Репозиторий
language	English
topic	2-Nitro-1H-benzo[f]chromenes Divergent transformations Naphtho[2,1-b]furans Pyran ring contraction
spellingShingle	2-Nitro-1H-benzo[f]chromenes Divergent transformations Naphtho[2,1-b]furans Pyran ring contraction Demidov, O. P. Демидов, О. П. Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction
description	The action of 2-(1-arylethylidene)malononitriles on 2-nitro-1H-benzo[f]chromenes in the presence of Et3N and MoO3•2H2O results in naphtho[2,1-b]furans containing an allylidenemalononitrile unit in the α-position. The reaction proceeds with contraction of the pyran ring via a cascade carba-Michael addition/retro-oxa-Michael reaction/tautomerization/SN2/oxidation process. In contrast, the reaction of 2-nitro-1H-benzo[f]chromenes with the cyclic Knoevenagel adduct derived from 1-indanone and malononitrile leads to dihydroindeno[1,2-c]xanthenes. The possibility of further transformations of naphtho[2,1-b]furan derivatives as useful precursors and their optical properties were also investigated.
format	Статья
author	Demidov, O. P. Демидов, О. П.
author_facet	Demidov, O. P. Демидов, О. П.
author_sort	Demidov, O. P.
title	Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction
title_short	Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction
title_full	Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction
title_fullStr	Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction
title_full_unstemmed	Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction
title_sort	divergent transformations of 2-nitro-1h-benzo[f]chromenes in reactions with alkylidenemalononitriles: access to naphtho[2,1-b]furans via base-mediated pyran ring contraction
publishDate	2024
url	https://dspace.ncfu.ru/handle/20.500.12258/26909
work_keys_str_mv	AT demidovop divergenttransformationsof2nitro1hbenzofchromenesinreactionswithalkylidenemalononitrilesaccesstonaphtho21bfuransviabasemediatedpyranringcontraction AT demidovop divergenttransformationsof2nitro1hbenzofchromenesinreactionswithalkylidenemalononitrilesaccesstonaphtho21bfuransviabasemediatedpyranringcontraction
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Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction

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